1-amino-2-nitrobenzene-4-sulfonic acid amides



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,Merian, All'schwil; Switzerland,assignor bymesne I assignments, to Saul& 'Co.,"Ne'war'k, N. J., as nominee of Fidelity Unipn, Trust Company,executive trustee under Sandoz Trust r N Drawing. Application February21, 1955 Serial No. 489,771

Claims priority, application SwitzerlanrLFebruary 22, 1 954- 5 Claims.((21. Only a few disperse dyestuffs are known dye acetate rayon inyellgw shades having sufiieient'fastness m wi hsta as a ele a es; emna mq witti The following examples, illustrate; the invention without in anyway limiting its scope. The proportions refer to parts by weight;temperatures are in degrees centigrade.

Example 1 ethoxybenzenm 3l-1:.2,pa,rtsof} L-chloro-Z-nitrobenzene-4-undergoing change of shade or bleeding on adjacent material. Theafiinity of these dyestuffs for acetate rayon, however, is insufiicient.

The present invention relates to disperse dyestuffs which have goodaffinity for acetate rayon. They dye this fiber in reddish yellow shadesof very good fastness to washing and excellent fastness to light and togas fumes. The dyestuffs are water-insoluble derivaties of l-amino-Z-nitrobenzene-4-sulfonic acid amide and correspond to the formula Theaforesaid derivatives of 1-amino-2-nitrobenzene-4' sulfonic acid amideare obtained by reacting 1 mol of a 1-halogen-2nitrobenzene-4-sulfonicacid amide which corresponds to the formula wherein x stands forchlorine or bromine, with 1 mol of an amine of the formula wherein R isas precedingly defined.

The reaction of the 1halogen-Z-nitrobenzene-4-sulfonic acid amides ofthe Formula I with the amines of the Formula II is best conducted atelevated temperatures. Water is an excellent reaction medium; a wettingagent may be added, or alternatively an organic solvent, e. g. ethanol,benzyl alcohol, benzene, toluene, etc. An addition of a suitableacid-binding agent such as sodium acetate, sodium carbonate or sodiumbicarbonate has a favourable influence on condensation in most cases.The same effect is achieved with an excess of the appropriate amine oramines.

The 1halogen-Z-nitrobenzene-4-sulfonic acid amides used as startingmaterials for performing this invention can be produced by therecognized methods, i. e. by treating 1halogen-Z-nitrobenzene-4-sulfonicacid halides with phenylamine under mild conditions. The l-chlcro-2-nitrobenzene-4-sulfonic acid-phenylamide e. g. has a melting point of85 C.

When converted into a dye preparation in the normal manner, it dyesacetate rayon and synthetic polyamide fibers from aqueous'dispersion inreddish yellow shades which are fast tolight and subliming. Dyeings onacetate ray-on are specially noteworthy for their outstanding fastnessto washing. Thus they withstand treatment in an equeous solutioncontaining 0.5% soap and 0.2% soda for 45 minutes at 71 (Wash Test No.3, 1953 Technical Manual and Year Book of the American Association ofTextile Chemists and Colorists, pages 91-92) without undergoing changeof shade or bleeding onto adjacent acetate and viscose rayon.

Example 2 10.4 parts of 1chloro-2-nitrobenzene-4-sulfonic acidphenylamide and 6 parts of 1-amino-4-(2'-hydroxy)- ethoxybenzene arestirred into 50 parts of water. The suspension is heated to boilingpoint, 3 parts of sodium bicarbonate added in portions, and the wholestirred for 4 hours at 100. The dyestuff gradually separates out insolid form and after cooling the mass is removed by filtration. Afterwashing and drying, a yellow-brown powder is obtained which can becrystallized to form orange colored needles having a melting point of140. It corresponds to the formula HO-HzC-HzQ-O-ONH-O-SOz-NHO Whenconverted'into a dye preparation in the normal way, the new dyestuffdyes acetate rayon from aqueous dispersion in reddish yellow shadeswhich are fast to light and subliming. The dyeings are characterized byvery good fastness to washing.

Example 3 A dyebath is prepared with 0.6 part of the dyestufi obtainedaccording to Example land dispersed with the aid of Turkey red oil, 6parts of a sulfonated fatty alcohol and 3000 parts of water. parts ofacetate rayon are entered at room temperature, the bath raised to 80within 1 hour and maintained at this level for another hour, at whichtime the dyeing process is completed. On removal the goods are rinsedand dried. To im rove the dispersion, the dyestuff can be ground priorto dyeing with suitable wetting, dispersing and emulsifying agents, andpreferably in the presence of inorganic salts, e. g. Glauber salt. Itcan also be intimately mixed in aqueous paste N01 1 iR-CHr-CHz-OONHOSOHIHO wherein R is a member selected from the group con-10 sisting of hydroxy and methoxyethoxy.

2. The 1-amino-2-nitrobenzcne-4-sulfonic acid amide which corresponds tothe formula 1 5. Acety1cellu1ose dyed with a compound defined in claim1.

References Cited in the file of this patent UNITED STATES PATENTSFischer et al. Nov. 12, 1940 McNalley et al June 10, 1947 Dickey et al.Apr. 5, 1949 Dickey et al Apr. 5, 1949 Kopp et al. May 2, 1950 FOREIGNPATENTS Germany Dec. 15, 1938 1 i N0) mo-o-H,c-mc-o-mo-mo-oQ-mxOsomnO 3.The 1-amin0-2-nitrobenzene-4-sulfonic acid amide which corresponds tothe formula 20 4. Hydrophobic fibers dyed with a compound defined 25 inclaim 1.

OTHER REFERENCES fischer: Berichte der Dcut., vol. 24 (1891), pages3793-95. Webster etaL: I. A. C. S, vol. 63 (1941), page 1928. Northey:The sulfonamides and Allied Compounds,

1948, pages 246, 247.

1. A 1-AMINO-2-NITROBENZENE-4-SULFONIC ACID AMIDE WHICH CORRESPONDS TOTHE FORMULA
 4. HYDROPHOBIC FIBERS DYED WITH A COMPOUND DEFINED IN CLAIM1.